This study examines the accuracy of large-eddy simulation (LES) to simulate the flow around a large irregular sloping complex terrain. Typically, real built up environments are surrounded by complex terrain geometries with many features. The complex terrain surrounding The Hong Kong University of Science and Technology campus was modelled and the flow over an uphill slope was simulated. The simulated results, including mean velocity profiles and turbulence intensities, were compared with the flow characteristics measured in a wind tunnel model test. Given the size of the domain and the corresponding constraints on the resolution of the simulation, the mean velocity components within the boundary layer flow, especially in the stream-wise direction were found to be reasonably well replicated by the LES. The turbulence intensity values were found to differ from the wind tunnel results in the building recirculation zones, mostly due to the constraints placed on spatial and temporal resolutions. Based on the validated mean velocity profile results, the flow-structure interactions around these buildings and the surrounding terrain were examined.